Aluminium lithium hydride → HCID 67261360, compound

HRID 79309Notes

Reaction equation

HRID 79309 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](OCC)=[O:14])[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([CH2:13][OH:14])[CH:10]=[N:9]2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 44558860ethyl 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 67261360HCID 67261360, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To ethyl 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate (8.31 g, 31.9 mmol) in THF (100 mL) at 0° C. was added lithium aluminum hydride (1.45 g, 38.3 mmol). The cold bath was removed and the reaction was stirred for 3 hours. The reaction mixture was diluted with Et2O (200 mL) and Celite (10 g) was added to the reaction mixture. The mixture was cooled to 0° C. and sodium sulfate decahydrate was cautiously added to quench the reaction, which was then filtered, and the filter pad was washed with EtOAc (100 mL) and concentrated to provide the desired product (5.26 g).

Workup

  1. customThe cold bath was removed
  2. additionThe reaction mixture was diluted with Et2O (200 mL) and Celite (10 g)
  3. additionwas added to the reaction mixture
  4. additionsodium sulfate decahydrate was cautiously added
  5. customto quench
  6. customthe reaction, which
  7. filtrationwas then filtered
  8. washthe filter pad was washed with EtOAc (100 mL)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a57c2180b57a44a2b6609ca0acbd1b6b
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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